


Men of Extraordinary Intellect

by Ultra



Series: Fixing A Hole [2]
Category: Gilmore Girls
Genre: Alternate Universe, Books, Boys Being Boys, Card Games, Drinking & Talking, F/M, Family Dynamics, Friendship, Gambling, Gen, Grandparents & Grandchildren, Love, New York City, Poker, Poker Nights, Post-Season/Series 07 AU, Unexpected Visitors
Language: English
Status: Completed
Published: 2019-10-09
Updated: 2019-10-09
Packaged: 2021-02-26 06:02:18
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,373
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21708673
Author URL: https://archiveofourown.org/users/Ultra/pseuds/Ultra
Summary: Richard Gilmore pays a surprise visit to Rory & Jess in NYC and spends an evening being one of the boys.
Relationships: Rory Gilmore/Jess Mariano
Series: Fixing A Hole [2]
Series URL: https://archiveofourown.org/series/1563886
Kudos: 28





	Men of Extraordinary Intellect

**Author's Note:**

  * For [GentleReader1](https://archiveofourown.org/users/GentleReader1/gifts).



> Originally written for GentleReader, based on her ideas, for her birthday.

“Jess? Could you please get that?” Rory yelled at the sound of the buzzer, trying in vain to fasten her shoe that seemed reluctant to comply. “It’s probably Lou. If you could tell her I’ll just be five minutes...”

Before she was hardly done giving instructions, Jess appeared in the bedroom doorway with a very weird look on his face.

“It’s not Lou,” he confirmed.

“So, the guys are early for poker night?”

Jess shook his head and then turned to walk away again, making Rory frown. With her shoe finally fastened, she straightened up, pulling at her dress as she went after him. She almost ran into his back half way across the short space of the living room.

“Be my guest,” he said, gesturing for her to answer the door when someone knocked.

Rory really wasn’t sure what she was expecting and gasped with surprise when she saw the truth.

“Grandpa. What are you doing here?” she asked, even as she gave him the biggest hug. “It’s so good to see you.”

“Well, what a wonderful welcome,” said Richard, hugging her back then kissing her cheek as they finally parted. “You’re certainly looking well, Rory,” he told her happily. “Now, in answer to your question, your grandmother had a very important event to attend for the DAR and left me home alone for the entire weekend. The thought suddenly occurred to me that my time could be more pleasantly spent in the company of my granddaughter and her charming young man. How are you, Jess?” he asked then, holding out a hand.

“Never better, sir,” he said, shaking hands politely. “Sorry, Richard,” he amended off the older man’s look. “You seem to be doing just fine yourself.”

“Indeed. I am in rude health, as my grandmother used to say,” he heartily agreed, “however, my timing seems to be less than appropriate. You are dressed to go out, Rory,” he noted, looking at her properly.

“Uh, yes, I am,” she admitted awkwardly. “A friend of mine from work, she’s attending this event. From what I can figure out it’s sort of a feminist movement that’s also charitable? Anyway, she needs me there to help fill a table... but I’m sure I could cancel.”

“Nonsense, nonsense.” Richard shook his head. “You should go and support your friend, most especially if she is also a work colleague. Those kinds of relationships should not be neglected,” he told her, every inch the sage businessman. “I can simply go to my hotel for tonight and perhaps call back tomorrow?”

“Oh, you don’t have to go,” Rory insisted, feeling bad about the whole situation.

She had seen her grandparents only a couple of times since she and Jess moved to New York, once at Christmas when they went back home for the occasion, and once when Emily and Richard insisted on seeing the apartment their granddaughter now called home. Unsurprisingly, Richard had been kind if not awkward, handing Rory extra money on the way out, while Emily dealt out the usual barely-veiled insults on just about everything. It was a real surprise to have Grandpa just show up like this but Rory didn’t mind it. The last thing she wanted was for him to feel like she wasn’t happy to see him.

“I’m guessing you don’t play poker?” she checked.

“Poker?” Richard echoed, looking from Rory to Jess, the latter of whom squirmed a little.

“The guys from Truncheon are in the city for a visit too,” he explained, hands stuffed in his pockets as he shifted in place. “We did all the business meeting stuff already today, so tonight is poker night. Obviously, you’re welcome to join us if you want to,” he said politely, undoubtedly hoping Richard would say no, Rory was sure on that.

Her grandfather bemused them both when he did the opposite.

“Well, if you’re sure I wouldn’t be intruding,” he said, shrugging off his coat.

“Not at all,” said Jess, looking to Rory for help, but unfortunately, she had none to give.

“I have to go,” she told him, though there was an added apology written in her eyes as she backed towards the door, grabbing her coat and purse as she went. “Have fun?” she added before ducking out to wait for Lou downstairs.

At the end of the day, Rory knew she could trust Jess not to say or do anything he shouldn’t in front of her grandfather, and vice versa, actually. With the guys from Truncheon coming over, talk was likely to be mostly book-related, when they weren’t concentrating on their card game, of course. Though they would doubtless be drinking, Jess wasn’t a sloppy drunk. He could hold his liquor, and his tongue, if necessary.

“Hey!” Lou called, hurrying to meet Rory mere seconds after she got down onto the street herself. “Sorry, am I late? They shut down a bunch of stops on the subway. It was anarchy down there.”

“Then it’s a good thing this event is only two blocks away.” Rory smiled. “We’ll walk... fast,” she suggested as they hurried along together.

“Are you okay, Rory?” Lou asked after a moment. “You have that frown line thing that you get when a story isn’t going right and you think you might miss a deadline.”

Rory opened her mouth to answer that but then a changed her mind. It would sound so stupid to admit her biggest worry was her grandfather spending time with her boyfriend and his business associates.

“Nope, I’m fine,” she said instead, deciding not to worry about it anymore.

(Yeah, like that was going to happen!)

* * *

Rory was tired and her head was pounding by the time she got home. It seemed Lou’s feminist charity event was heavy on the (extreme) feminism, light on the charity. Too many angry speeches and female outrage for Rory’s taste. In some ways, she thought she would’ve been happier at the guys’ poker game, until she remembered that her grandpa was in the middle of all that.

Letting herself into the building, she rode the elevator up to the third floor and then stopped by the apartment door. There was a serious amount of very loud laughter happening inside, which seemed like it should be a good thing, especially since the person laughing loudest was Richard, if she wasn’t mistaken.

Quietly opening up the door, Rory crept in, hovering behind the nearest bookcase in an attempt to catch the guys in their natural state before she dived in.

“It was the most absurd thing. He really thought he could drown me out with his ridiculous boombox, but no, I won the day! To this day, I cannot hear that Cher person singing without chuckling to myself.”

“You’re a true hero of real culture, Mr Gilmore,” said Brendan, raising his beer bottle in some kind of toast.

“Oh, please, as I told you, it’s Richard,” he insisted. “I do think a man should always be on first name terms with the person who has taken so much of his money.”

Another eruption of laughter at the good joke, even from Bren, poor guy. He probably couldn’t afford to lose too much. After all, he was only Jess’ assistant and the New York branch of Truncheon hadn’t exactly got to the point of turning a great profit yet. Rory couldn’t see where all the chips were on the table from her hiding place, but she would be willing to bet that Jess had made a good few bucks, and apparently, her grandfather had too.

What she could see was that Richard had a cigar between his teeth and the jacket of his pristine three-piece suit was hanging on the back of a mismatched chair, the sleeves of his shirt rolled back to his elbows that were resting on a littered IKEA table. He looked strangely like one of the guys, save for the fact his beer had been poured into a glass while the rest drank from bottles.

“Now, no more distractions, gentlemen,” he said then. “You’re all light on your stake, you know?”

As the guys anted up, Rory decided it was probably best to let them know she was there. She closed the apartment door with a loud clang and strolled into the living room as if she just arrived, to the usual round of cheery greetings from the guys.

“Wow, look at you.” Chris smiled as he took in her dressed-up appearance. “Jess, I swear, she’s just too good for you.”

“Like I don’t know that already.” Jess rolled his eyes, shifting his gaze from the game to look at Rory. “Fun night?”

“Don’t ask,” she told him, moving closer and putting her arm around his shoulders as she checked out his cards. “How about you?”

“I’m doing okay,” he said, nodding his head. “Your grandfather, however, is cleaning up.”

“I am doing rather well, aren’t I?” he said with a comically evil laugh that made Rory giggle too.

“Don’t you just fit right in as one of the guys?”

“I do indeed,” Richard noted. “However, I believe that is only because this is such a fine group of young men. All very intelligent and well-spirited, not at all what one expects from young people these days.”

“Rory, we’re giving due consideration to adopting your grandfather as one of own,” said Matthew too seriously. “Or more accurately, we would really like him to adopt all of us.”

“At least then I might inherit some of my money back one day.” Bren sighed, throwing down his cards and declaring he had to fold again.

The hand continued a little longer with Richard eventually winning to a chorus of groans from the rest.

“Well, given that Rory’s home, and if we keep playing, I’m not going to make rent this month,” Chris noted, “I think now might be a good time to call it a night.”

“Agreed,” said Jess, gathering up the cards and prompting the guys to get their money figured out between them too.

“I have had the most splendid evening,” Richard declared when they were all more or less ready to go. “Rory, it was of course disappointing not to see more of you, but I must admit, it has been a truly enjoyable event all the same. I can’t remember when I was in such good company. All the men at my club are so old and stuffy. I much prefer your friends to my own acquaintances.”

“You’re welcome anytime, Grandpa,” Rory assured him. “Right, Jess?”

“Sure, we play every month or so, when the guys are in town,” he explained to Richard. “I could give you a call when we fix the date for the next one.”

“Well, that would be wonderful.” Richard smiled. “And Matthew, you be sure to send me that novella. I’ll be happy to look over it for you.”

“Novella?” Rory frowned.

“That thing with all the Latin that Randall sent me a couple of weeks ago,” Matthew reminded her. “I can’t edit what I can’t understand,” he said, shrugging his shoulders. “However, Richard has offered to help me out.”

The next thing Rory knew the guys were offering to walk her grandfather to the subway, only for him to insist on getting a cab for them to share. After all, he could well afford it after winning so much of their money!

“Rory, my dear, we’ll catch up tomorrow,” he promised, leaning down to kiss her cheek. “And Jess, thank you for a most excellent evening,” he said, shaking his hand with gusto before finally leaving.

Rory felt so shocked as the four guys headed out the door together, Chris asking something about a long-ago Chuck Berry concert that Richard was only too happy to tell him more about. The door closed behind them and she couldn’t help but laugh.

“I feel like I entered Bizarro World,” she admitted aloud.

“I noticed you entered five minutes before you pretended to also.” Jess smirked as she looked wide-eyed at him. “What? You wanted to check we weren’t in some kind of pistols-at-dawn situation before you strolled in?”

“No, nothing like that.” Rory rolled her eyes. “I was just curious when I heard laughter. You have to admit, my grandfather fitting into poker night with you and the guys? Not an expected scenario.”

“Point taken.” Jess nodded, rearranging the chairs back to where they usually were. “But actually, it was all pretty cool, except how much money we all lost to Gambling Gilmore, and before you complain about the choice of nickname, I didn’t come up with that. Apparently, it’s what your grandpa was known as for a while in college.”

“Grandpa was a card sharp?”

“Pretty much, from what he said. I believe it too. He took Bren for practically every cent he had. Even I was on the ropes a couple of times.”

“Wow.” Rory shook her head in wonder.

“Wasn’t just cards either. I mean, he has some stories to tell.”

“I do know Grandpa likes to spin a good yarn to an audience.”

“Yeah, but he actually listens too, and he’s not all... well, you know how your grandma is sometimes with the holier-than-thou attitude?”

“Do I ever?” Rory sighed. “Grandpa’s never really been as bad as her that way.”

“I get that,” Jess agreed, deciding he was happy that he had cleaned up as much as he needed to for tonight. He turned around to face Rory then, pulling her into his arms. “So, seems like I made a new buddy out of your grandpa. Kind of weird.”

“Kind of is,” she agreed, her arms sliding up around his neck. “I like it though. He means so much to me, and you mean so much to me. I really appreciate you making an effort, you know?”

“Oh, yeah?” he said, kissing her cheek then behind her ear. “How much?”

“Hmm, a lot,” Rory confessed as his lips found the spot on her neck that made her knees go weak. “A _very_ lot.”

“Sounds good,” Jess said softly, never letting up his delicious assault on her senses.

Funnily enough, they didn’t talk, or even think, about Rory’s grandpa for the rest of the night.


End file.
